反応 #52854

反応方程式

4,4-dimethyl-7-bromo-3,4-dihydronaphthalen-1(2H)one

7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1-one

Compound G

7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1-one

1-ethoxyvinyltributyltin

hydrochloric acid

EVTB

→

4,4-Dimethyl-7-acetyl-3,4-dihydronaphthalen-1(2H)-one

溶媒

THF

反応条件

後処理

1. 1
   workup.ADDITIONwere added
2. 2
   温度refluxed for an additional 24 h
3. 3
   workup.ADDITIONwas added
4. 4
   抽出the mixture was extracted with ether (3×50 mL)
5. 5
   洗浄the combined organic layer was washed with water (10 mL), 10% sodiumbicarbonate (10 mL), brine (10 mL)
6. 6
   乾燥dried with magnesium sulfate
7. 7
   その他Solvent was removed under reduced pressure
8. 8
   その他after purification by flash chromatography the title compound
9. 9
   その他was obtained as a white solid

実験手順

A solution of 4,4-dimethyl-7-bromo-3,4-dihydronaphthalen-1(2H)one (Compound G) (1.78 g, 7 mmol), 1-ethoxyvinyltributyltin (EVTB) (3.3 g, 9.12 mmol), bis(triphenylphosphine)palladium(II)chloride (260 mg, 0.23 mmol) in THF (25 mL) was refluxed for 24 h under argon atmosphere. To the reaction, additional EVTB (1.5 g, 4.1 mmol) and bis(triphenylphosphine)palladium(I)chloride (200 mg, 0.2 mmol) were added and the mixture was and refluxed for an additional 24 h. The reaction mixture was cooled to room temeperature and 10% hydrochloric acid (10 ml) was added. After 10 min, the mixture was extracted with ether (3×50 mL), the combined organic layer was washed with water (10 mL), 10% sodiumbicarbonate (10 mL), brine (10 mL), dried with magnesium sulfate. Solvent was removed under reduced pressure, and after purification by flash chromatography the title compound was obtained as a white solid.

出典